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Synfacts 2006(11): 1094-1094  
DOI: 10.1055/s-2006-949388
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Paroxetine

Contributor(s): Philip Kocienski
S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen*
Aarhus University, Denmark
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Publikationsdatum:
24. Oktober 2006 (online)

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Significance

A six-step synthesis of the serotonin uptake inhibitor (-)-paroxetine features an organocatalytic asymmetric conjugate addition of dibenzyl malonate to α,β-unsaturated aldehyde A mediated by the proline-derived catalyst B. 15 examples are given with yields generally in the range 72-93% (er > 93:7).